5-(3-nitrophenyl)-1,8,8-trimethyl-3,7,8,9,10-pentahydropyrimido[4,5-b]quinoline-2,4,6(5H)-trione | 1251466-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(3-nitrophenyl)-1,8,8-trimethyl-3,7,8,9,10-pentahydropyrimido[4,5-b]quinoline-2,4,6(5H)-trione
• 英文别名: 1,8,8-Trimethyl-5-(3-nitrophenyl)-5,7,9,10-tetrahydropyrimido[4,5-b]quinoline-2,4,6-trione
• CAS: 1251466-89-3
• 化学式: C₂₀H₂₀N₄O₅
• 分子量: 396.403
• InChiKey: FQPCEOHADLRWOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氨基-1-甲基尿嘧啶 、 间硝基苯甲醛 、 5,5-二甲基-1,3-环己二酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以59%的产率得到5-(3-nitrophenyl)-1,8,8-trimethyl-3,7,8,9,10-pentahydropyrimido[4,5-b]quinoline-2,4,6(5H)-trione
  参考文献：
  名称：

  Facile Synthesis, Pure DFT Calculations, and PM3 Semiempirical MO Method Validation of Regiospecificity of Novel 1,4-Dihydropyrido[2,3-d]pyrimidine Derivatives

  摘要：

  Reaction of 6-aminothiouracil (or uracil) with equimolar amounts of different ketones or diketones and the appropriate aromatic aldehydes afforded di- and tricyclic linear pyrido[ 2,3-d] pyrimidine derivatives 4, 6-12, 14, 16-18, 20, and 21, and pyrimido[4,5-b] quinoline derivatives 15 and 19 in good yields. The regiospecificity, which led to the formation of compound 4 not 5, was validated using ab initio at the HF/6-31G(+)(d,p) level and pure density functional theory (DFT) calculations using BLYP energy functional and the basis set DNP via studying the thermodynamics of their possible conformers and regioisomers. In addition, the total energy of the transition state was calculated for compounds 12 and 13 to determine whether the reaction products were thermodynamically or kinetically controlled. Hence, the linear structures and the regiospecificities of the reactions for the structures reported in this article were established by elemental analysis, spectral data, ab initio calculations, pure DFT, and PM3 parameters.

  DOI：

  10.1080/00397910903534015

文献信息

• Facile Synthesis, Pure DFT Calculations, and PM3 Semiempirical MO Method Validation of Regiospecificity of Novel 1,4-Dihydropyrido[2,3-d]pyrimidine Derivatives
  作者：A. El-Shafei、A. A. Fadda、S. Bondock、A. M. Khalil、Eman H. Tawfik

  DOI：10.1080/00397910903534015

  日期：2010.8.16

  Reaction of 6-aminothiouracil (or uracil) with equimolar amounts of different ketones or diketones and the appropriate aromatic aldehydes afforded di- and tricyclic linear pyrido[ 2,3-d] pyrimidine derivatives 4, 6-12, 14, 16-18, 20, and 21, and pyrimido[4,5-b] quinoline derivatives 15 and 19 in good yields. The regiospecificity, which led to the formation of compound 4 not 5, was validated using ab initio at the HF/6-31G(+)(d,p) level and pure density functional theory (DFT) calculations using BLYP energy functional and the basis set DNP via studying the thermodynamics of their possible conformers and regioisomers. In addition, the total energy of the transition state was calculated for compounds 12 and 13 to determine whether the reaction products were thermodynamically or kinetically controlled. Hence, the linear structures and the regiospecificities of the reactions for the structures reported in this article were established by elemental analysis, spectral data, ab initio calculations, pure DFT, and PM3 parameters.